How I Dress Now: Lyle Lovett

My take on how to dress is this: Wear what you want to wear. Do what you want to do. Be who you are. Pick out your own clothes. Be a man. And if that's too much to ask, as it almost always is for me, think of someone you consider to be a man and pretend to be like him. I pretend to be like my dad.

My father never wavered in the mornings as he stared into his closet. He plunged his arm inside with confidence and came out with just the right suit or shirt or slacks. My first lessons in getting dressed, in figuring out that it somehow matters what you decide to wear on a given day, came from watching him, from watching how intently he studied his image in the mirror and meticulously tied the full-Windsor knot he preferred, how carefully he folded down the collar of his neatly pressed shirt, and how, when he had finished, he would sweetly press his freshly shaved face against mine. "See?" he'd say. "Smooth," telling me, in effect, that's how you do it.

Advertisement - Continue Reading Below

How my dad dressed for work was important. He (and my mom) worked for 40 years for the Humble Oil and Refining Company, the Texas-based company that merged with Standard Oil of New Jersey and became Exxon in the '70s. Humble was a conservative place. It wouldn't have served him to have pushed the fashion envelope at work, even in the '70s — to have worn a psychedelic tie or scarf, or too wide of a lapel, much less bell-bottoms or a white belt or white shoes or a leisure suit. It wouldn't have served him to do anything to call attention to himself for any reason other than his exemplary work. He knew that. Dad often told me, "My job is to help my boss do his job and make him look good."

This fall, Lovett is joining with Hamilton Shirts to update the company's classic western shirt. Lyle Lovett Western ($265) by Hamilton Shirts, hamiltonshirts.com

Most Popular

That was my dad's objective. Everything about the way he conducted himself was to communicate support for his superiors and respect for his coworkers. The way he dressed was his starting point in that communication. So now, when I stare into my closet, I think, How I dress depends on what I want to say.

You're saying something with your appearance whether you mean to or not, so you may as well mean to. For example, on a weekend morning, you might actually mean to say, "It's Saturday and I don't care how I look, and I don't care what you think of how I look, and I don't care if I ever have sex again."

You might really mean that. But you'd better think about what you're saying, because everyone else is. The idea that we humans are good-natured, politically correct, nonjudgmental beings is pure fantasy. We are, at the very least, judgmental.

My next lessons in how to dress came from classmates in parochial school. The time-honored, behavior-modifying method of ridiculing and instilling a sense of shame were not spared at Trinity Lutheran School in Klein, Texas. "A sweater," a boy said in a loud voice in front of the whole class as I walked into my second-grade classroom on an early October day and heard everyone laughing. In my defense, my desk was by the always-open window, and it was getting cooler, and it was a new sweater I was eager to wear — an off-white cable-knit V-neck. I loved that sweater. I didn't wear it again until it was freezing, three months later.

In my early 20s, Searcy Bond, who owned a hamburger joint I used to play at on Sunday nights, once asked me if I'd lost a bet. I asked him what he meant, and he pointed at my shirt and suggested that I'd been forced to wear it as payment for a wager gone wrong. Why would anyone wear a shirt like that if they didn't have to was his implication. But that's how you learn. Ridicule and shame don't get much of a chance in these sensitive times, which makes learning about how to dress that much more difficult.

Fashion is communication, plain and simple. I don't mean to sound as though I'm telling you something you don't already know, because any self-respecting man with even a little common sense knows exactly what he's saying and to whom he's saying it as he gets dressed in the morning. We all wear uniforms of sorts that allow us to be accepted. There's no shame in that. That we have the gumption to clean up and, as we stare into our closet, care about how we'll look shows we're trying to put our best foot forward.